Steam distillation of fennel oil from fennel seed

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1 University of Leipzig, Faculty of Chemistry and Mineralogy Institute of Organic Chemistry Advanced Practical Course in Organic Chemistry WS 2012/2013 Leipzig, October 5, 2012 Steam distillation of fennel oil from fennel seed Students: Supervisor: Martin Übler, Mert Berk, Tony Zielke and written by Marcel Schlegel Prof. Dr. Sicker 1 Introduction Fig. 1: Fennel seeds [1] Fennel is a member of the family Apiaceae (formerly the Umbelliferae) and known as a vegetable, spice and medicinal plant. Especially the seeds (Fig. 1) containing the

2 essential oils with the highly aromatic flavour are used for culinary and medicinal applications. Fennel tea is used to promote a healthy appetite and good digestion as well as to relieve abdominal cramps, upset stomach, colic or bloating. [1] Important ingredients of the fennel oil are mainly trans-anethole 1 and fenchone 3. [1] The purpose of the experiment is to obtain fennel oil from fennel seeds using steam distillation, to identify the yield and to characterise the composition of the components using 1 H-NMR spectroscopy Fig. 2: Structures of trans-anethole 1, estragole 2 and fenchone 3 2 Experimental part 250 g of Fennel seeds were extracted using steam distillation and the distillate obtained (2 x 750 ml) was separated into two 1 L flasks. The white emulsions were transferred into two 1 L separation funnels and extracted with each 5 x 100 ml methyl-tert-butylether. The organic phases were combined and dried using MgSO4. Subsequently, the solvent was removed under reduced pressure. A pale yellow, oily liquid was obtained in 2.4 g (1 %) yield. 3 Characterisation The complete 1 H-NMR spectrum of the fennel oil is shown in Fig. 3. Although there are many signals between 1 and 10 ppm the chemical shifts of trans-anethole 1 are exposed very well. For that reason trans-anethole 1 is apparently the main component. Furthermore, the 1 H-NMR spectrum reveals some smaller signals in the field of aromatic and olefinic protons that are similar to those of trans-anethole 1. Due to [3] the signals correspond to estragole 2, a compound distinguished from trans-anethole 1 by the

3 position of the double bond. In the aliphatic region there are some chemical shifts between 1.0 and 2.2 ppm that, compared to [4], belong to fenchone 3 since it contains no aromatic or olefinic protons. Fig. 3: 1 H-NMR spectrum of fennel oil: signals of trans-anethole 1 (A), estragole 2 (E) and fenchone 3 (F)

4 trans-anethole 1 (A): 1 H-NMR (400 MHz, CDCl3) δ [ppm] = 1.88 (dd, 3H, 3 JHH=6.6 Hz, 4 JHH=1.7 Hz, CH3), 3.81 (s, 3H, OCH3), 6.12 (dq, 1H, 3 JHH=15.6 Hz, 3 JHH=6.6 Hz, H-9), 6.37 (dq, 1H, 3 JHH=15.7 Hz, 4JHH=1.8 Hz, H-8), (m, 2H, H-2/6), (m, 2H, H-3/5). Estragole 2 (E): 1 H-NMR (400 MHz, CDCl3) δ [ppm] = 3.36 (d, 2H, 3 JHH=6.7 Hz, CH2), 3.89 (s, 3H, OCH3), (m, 2H, H-10), (m, 1H, H-9), (m, 2H, Ar-H), (m, 2H, Ar-H). Fenchone 3 (F): 1 H-NMR (400 MHz, CDCl3) δ [ppm] = 1.07 (s, 6H, H-8/9), 1.18 (s, 3H, H-10), (m, 6H, H-5/6/7), (m, 1H, H-4). The composition of the three components shown in the 1 H-NMR spectrum can be determined by the integrals of the single proton signals of trans-anethole 1 (A) at 6.37 ppm, estragole 2 (E) at ppm and fenchone 3 (F) at ppm. According to the formula = fennel oil contains 81 % of trans-anethole 1, 16 % of estragole 2 and 3 % of fenchone 3. 4 Discussion Steam distillation is an excellent method to obtain fennel oil from fennel seeds with its aromatic flavour of essential oils. Although it seemed obvious that fenchone should be the principal ingredient in fennel seeds because of the equal prefix fen in the name the 1 H-NMR spectrum (Fig. 3) reveals the contrary. According to the variety of signals three main compounds were assigned. Trans-anethole 1 was identified as major component with an amount of 81 %, conclusively. Since the remaining signals are small in comparison to those of trans-anethole 1 they are not simply associated with other compounds. Nevertheless, the regioisomer estragole 2 (16 %) was detected as a second possible ingredient. Whereas the chemical shifts assort

5 well with those of reference [3] there are some other signals, not shown in Fig. 3, like a doublet at 7.86 ppm that could belong to estragole 2 because of its integral and a singlet at 9.90 ppm. However, any other compounds showing signals in these spectroscopic areas were not found according to the ingredients of fennel oil. For that reason it is not unequivocally established that there could not be another compound unassigned or the compound detected was estragole 2. Considering the aliphatic region of the 1 H-NMR spectrum fennel oil contains a small amount of fenchone 3 (3 %). Most signals coincide with the spectroscopic data of reference [4]. However, as well as in estragole 2 there are some signals unassigned, especially between and 1.83 ppm. Additionally, a doublet at 1.44 ppm according to [4] was not found in Fig. 3. Summarising, fennel oil is obviously composed of 81 % of trans-anethole 1, 16 % of estragole 2 and 3 % of fenchone 3 corresponding to 1 H-NMR spectroscopy. Outlook In order to obtain more exact results all components could be separated using gas chromatography and then compared with a data base containing retention values of usual volatile components of aromatic plants, or even a combination of HPLC-MS could be used for separation and MS measurement prior to matching with corresponding data bases. 5 Literature [1] (October 5, 2012) [2] S. Berger, D. Sicker, Classics in Spectroscopy: Isolation and Structure Elucidation of Natural Products, 1 st ed., WILEY-VCH Verlag & Co. KGaA, Weinheim, 2009, 136. [3] C. M. R. Volla, D. Marković, S. R. Dubbaka, P. Vogel, Eur. J. Org. Chem. 2009, 36, [4] A. Guerrini, G. Sacchetti, M. Muzzoli, G. M. Rueda, A. Medici, E. Besco, R. Bruni, J. Agric. Food Chem. 2006, 54, Purification and spectroscopy of estragole are also described in: A. Prasse, Bachelorarbeit, 2009, University of Leipzig

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